Dimethylformamide → 4-cyano-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

HRID 559502Notes

Reaction equation

HRID 559502 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:26][O:27][CH3:28].C[N:30](C=O)C>O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:26][O:27][CH3:28])[C:14]2[S:15][CH:16]=[CH:17][N:18]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)#[N:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 210825294-Acetyl-n-(thiazol-2-yl)benzenesulfonamide

Product 1

HCID 670014474-cyano-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 4-acetyl-N-thiazol-2-yl-benzenesulfonamide (10 mmol) and potassium carbonate (15 mmol) in DMF (30 mL) was added chloro-methoxy-methane (10 mmol) and the mixture was stirred for 4 h. The reaction mixture was diluted with water (30 mL) and the resulting mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography to give 4-cyano-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (5.2 mmol) as a white solid.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-bd905ec12b7c40eaac587f50a0bdb360
Source dataset
uspto-grants-2011_11
Patent number
US08063080B2

Reaction notes

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